Highly cis- and enantioface-selective cyclpropanation using (R,R)-Ru- salen complex: Solubility dependent enantioface selection

Tatsuya Uchida; Ryo Irie; Tsutomu Katsuki

doi:10.1055/s-1999-2955

Highly cis- and enantioface-selective cyclpropanation using (R,R)-Ru- salen complex: Solubility dependent enantioface selection

Tatsuya Uchida, Ryo Irie, Tsutomu Katsuki

Division for Experimental Natural Science

Research output: Contribution to journal › Article › peer-review

56 Citations (Scopus)

Abstract

The reaction of styrene and t-butyl α-diazoacetate in the presence of (R,R)-(ON⁺)(salen)ruthenium(II) complex 1 under the irradiation of incandescent light in THF gave the corresponding (IS,2R)- cyclopropanecarboxylate with high stereoselectivity of 99% ee (cis: trans = 96:4), while the same reaction in hexane gave the enantiomeric (1R,2S)- cyclopropanecarboxylate preferentially (83% ee, cis: trans = 68:32).

Original language	English
Pages (from-to)	1793-1795
Number of pages	3
Journal	Synlett
Issue number	11
DOIs	https://doi.org/10.1055/s-1999-2955
Publication status	Published - 1999

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1055/s-1999-2955

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title = "Highly cis- and enantioface-selective cyclpropanation using (R,R)-Ru- salen complex: Solubility dependent enantioface selection",

abstract = "The reaction of styrene and t-butyl α-diazoacetate in the presence of (R,R)-(ON+)(salen)ruthenium(II) complex 1 under the irradiation of incandescent light in THF gave the corresponding (IS,2R)- cyclopropanecarboxylate with high stereoselectivity of 99% ee (cis: trans = 96:4), while the same reaction in hexane gave the enantiomeric (1R,2S)- cyclopropanecarboxylate preferentially (83% ee, cis: trans = 68:32).",

author = "Tatsuya Uchida and Ryo Irie and Tsutomu Katsuki",

year = "1999",

doi = "10.1055/s-1999-2955",

language = "English",

pages = "1793--1795",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "11",

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T1 - Highly cis- and enantioface-selective cyclpropanation using (R,R)-Ru- salen complex

T2 - Solubility dependent enantioface selection

AU - Uchida, Tatsuya

AU - Irie, Ryo

AU - Katsuki, Tsutomu

PY - 1999

Y1 - 1999

N2 - The reaction of styrene and t-butyl α-diazoacetate in the presence of (R,R)-(ON+)(salen)ruthenium(II) complex 1 under the irradiation of incandescent light in THF gave the corresponding (IS,2R)- cyclopropanecarboxylate with high stereoselectivity of 99% ee (cis: trans = 96:4), while the same reaction in hexane gave the enantiomeric (1R,2S)- cyclopropanecarboxylate preferentially (83% ee, cis: trans = 68:32).

AB - The reaction of styrene and t-butyl α-diazoacetate in the presence of (R,R)-(ON+)(salen)ruthenium(II) complex 1 under the irradiation of incandescent light in THF gave the corresponding (IS,2R)- cyclopropanecarboxylate with high stereoselectivity of 99% ee (cis: trans = 96:4), while the same reaction in hexane gave the enantiomeric (1R,2S)- cyclopropanecarboxylate preferentially (83% ee, cis: trans = 68:32).

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DO - 10.1055/s-1999-2955

M3 - Article

AN - SCOPUS:0032705876

SN - 0936-5214

SP - 1793

EP - 1795

JO - Synlett

JF - Synlett

IS - 11

ER -

Highly cis- and enantioface-selective cyclpropanation using (R,R)-Ru- salen complex: Solubility dependent enantioface selection

Abstract

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